Water → 1,1′-[4,8-Bis[(2-ethylhexyl)oxy]benzo[1,2-b:4,5-b′]dithiophene-2,6-diyl]bis[1,1,1-trimethylstannane]

HRID 2195101Notes

Reaction equation

HRID 2195101 reaction equation
[CH2:1]([CH:7]([CH2:39][CH2:40][CH2:41][CH2:42]CCCC)[CH2:8][O:9][C:10]1[C:18]2[S:19][CH:20]=[CH:21][C:17]=2[C:16]([O:22][CH2:23][CH:24]([CH2:33][CH2:34]CCCC)[CH2:25][CH2:26][CH2:27][CH2:28]CCCC)=[C:12]2[S:13][CH:14]=[CH:15][C:11]=12)[CH2:2]CCCC.C([Li])CCC.[CH3:52][Sn:53](Cl)([CH3:55])[CH3:54].O>C1COCC1>[CH2:1]([CH:7]([CH2:39][CH2:40][CH2:41][CH3:42])[CH2:8][O:9][C:10]1[C:18]2[S:19][C:20]([Sn:53]([CH3:55])([CH3:54])[CH3:52])=[CH:21][C:17]=2[C:16]([O:22][CH2:23][CH:24]([CH2:33][CH3:34])[CH2:25][CH2:26][CH2:27][CH3:28])=[C:12]2[S:13][C:14]([Sn:53]([CH3:55])([CH3:54])[CH3:52])=[CH:15][C:11]=12)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 14016Trimethyltin chlorideHCID 59609194HCID 59609194, compoundHCID 178418339Butyllithium

Product 1

HCID 582610831,1′-[4,8-Bis[(2-ethylhexyl)oxy]benzo[1,2-b:4,5-b′]dithiophene-2,6-diyl]bis[1,1,1-trimethylstannane]Yield 63.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

4,8-Bis[(2-hexyldecyl)oxy]-benzo[1,2-b:4,5-b′]dithiophene (0.80 g, 1.19 mmol) was dissolved in dry THF (10 mL) under nitrogen. The solution was cooled to −70° C. and butyllithium (1.0 mL, 2.M solution in hexanes, 2.5 mmol) was added dropwise. The reaction was allowed to warm to room temperature over 2 hours and cooled back to −78° C. Trimethyltin chloride (0.61 g, 3.0 mmol) was added. The reaction was allowed to warm to room temperature and stirred under nitrogen overnight. Water (50 mL) was added and the reaction was extracted with ether. Organic layer was separated and dried over Na2SO4. Solvent was removed under vacuum. To the residue was added ethanol (10 mL) and the suspension was stirred overnight. The resulting white solids were collected by filtration and dried under vacuum to afford the product 4,8-bis[(2-ethylhexyl)oxy]-2,6-bis(1,1,1-trimethyl-stannanyl)benzo[1,2-b:4,5-b′]dithiophene (0.58 g, 49%). 1H NMR (CDCl3, 500 MHz) δ=7.52 (m, 2H), 4.17 (d, J=5.0 Hz, 4H), 1.86 (m, 2H), 1.67 (m, 4H), 1.28-1.55 (m, 44H), 0.86 (m, 12H), 0.55 (m, 18H).

Workup

  1. temperatureto warm to room temperature over 2 hours
  2. temperaturecooled back to −78° C
  3. temperatureto warm to room temperature
  4. extractionthe reaction was extracted with ether
  5. customOrganic layer was separated
  6. dry with materialdried over Na2SO4
  7. customSolvent was removed under vacuum
  8. additionTo the residue was added ethanol (10 mL)
  9. stirringthe suspension was stirred overnight
  10. filtrationThe resulting white solids were collected by filtration
  11. customdried under vacuum

Sources & evidence

ORD record
ord-b1d98699121746448fe568694eeb90e5
Source dataset
uspto-grants-2012_12
Patent number
US08334456B2

Reaction notes

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